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Puerto Rico Cruises Starting In October 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2026, 2027 or 2028, we have 29 unique cruise itineraries and 137 departures available, operated by seven of the world's leading cruise lines departing in October.
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29 Cruises (137 Departures)
29 Cruises (137 Departures)
Departures
Duration
8 Days
20 Days
Countries Visited
Start & End Cities
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Price
$800pp
$30,840pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Inside
$1,745
Oceanview
$1,994
Balcony
$1,994
Suite
$6,707
From (Per Person)
A$1,745
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,284
Oceanview
$1,432
Balcony
$1,789
Suite
$6,669
From (Per Person)
A$1,284
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,561
Oceanview
$1,888
Balcony
$2,175
Suite
-
From (Per Person)
A$1,561
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,264
Oceanview
$1,373
Balcony
$1,699
Suite
-
From (Per Person)
A$1,264
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$895
Oceanview
$974
Balcony
$1,061
Suite
$1,716
From (Per Person)
A$895
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,002
Oceanview
$1,338
Balcony
$1,655
Suite
$2,309
From (Per Person)
A$1,002
Save 24
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,555
Oceanview
$1,650
Balcony
$1,746
Suite
$3,887
From (Per Person)
A$1,555
Save 1,225
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Allure of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,516
Oceanview
$1,558
Balcony
$1,535
Suite
$5,352
From (Per Person)
A$1,516
Save 32
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,783
Oceanview
$1,923
Balcony
$2,190
Suite
$4,398
From (Per Person)
A$1,783
Save 1,255
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Icon Of The Seas
Departures: Aug 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,785
Oceanview
$2,031
Balcony
$2,250
Suite
$3,055
From (Per Person)
A$1,785
Save 88
Per Person
View Trip
10 Day New York to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 26 October 2026
Visits: USA, Bermuda, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$4,995
Balcony
$5,872
Suite
$6,262
From (Per Person)
A$4,995
Save 1,605
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Operator: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,766
Oceanview
$2,129
Balcony
$2,798
Suite
$7,476
From (Per Person)
A$1,766
Save 901
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,750
Suite
$3,607
From (Per Person)
A$865
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,355
Oceanview
$1,527
Balcony
$1,900
Suite
$4,614
From (Per Person)
A$1,355
Save 794
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,060
Oceanview
$1,144
Balcony
$1,598
Suite
$2,721
From (Per Person)
A$1,060
Save 679
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,717
Oceanview
$1,820
Balcony
$1,922
Suite
$5,376
From (Per Person)
A$1,717
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,052
Oceanview
$1,092
Balcony
$1,834
Suite
$2,245
From (Per Person)
A$1,052
Save 869
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,093
Oceanview
-
Balcony
$1,271
Suite
$1,687
From (Per Person)
A$1,093
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,681
Suite
$10,156
From (Per Person)
A$2,681
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,591
Suite
$12,118
From (Per Person)
A$2,591
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (5)

10 Days (9 Nights) New York to San Juan
Operator: Azamara
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,545
Oceanview
$2,945
Balcony
$3,597
Suite
$6,138
From (Per Person)
A$2,545
Save 164
Per Person
View Trip
20 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

20 Days (19 Nights) Genoa to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$2,315
Oceanview
$2,444
Balcony
$2,830
Suite
-
From (Per Person)
A$2,315
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,562
Oceanview
$2,869
Balcony
$3,413
Suite
$5,779
From (Per Person)
A$2,562
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,741
Suite
$10,658
From (Per Person)
A$2,741
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,468
Oceanview
$1,665
Balcony
$1,726
Suite
$4,102
From (Per Person)
A$1,468
Save 963
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departure: 04 October 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,553
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,553
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,143
Oceanview
$1,311
Balcony
$1,509
Suite
$2,083
From (Per Person)
A$1,143
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,129
Oceanview
$1,295
Balcony
$2,240
Suite
$3,540
From (Per Person)
A$1,129
Save 668
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,661
Oceanview
$1,734
Balcony
$2,078
Suite
$6,287
From (Per Person)
A$1,661
Save 822
Per Person
View Trip
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